Benzoyl chloride → HCID 12940182, compound

Participants

Reaction Steps

A mixture of 2-amino-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-2H-benzo[a]quinolizine (5.0 g., 0.019 mole), 20% NaOH (25 ml) and 150 ml of benzene was cooled in an ice bath and benzoyl chloride (2.7 g, 0.019 mole) in 10 ml of benzene was added dropwise with stirring. The mixture was stirred in the cold for 30 minutes and at room temperature for 1 hour. The solid was collected, dissolved in chloroform, washed with water, dried (MgSO4) and concentrated in vacuo. The residue (5 g) was chromatographed over silica gel eluting with benzene-methanol (9:1). The free base (3.7 g) was converted to the HCl salt with hydrogen chloride in a mixture of 2-propanol and methanol. The solution was concentrated in vacuo and the residue was crystallized from methanol-ether. The resulting solid was recrystallized from ethanol-ether to yield 3.0 g of the desired product, m.p. 250°-1°. This product comforms to Formula II where R1 and R2 are --OCH3, R3 is H and R4 is ##STR36##

Provenance & Evidence